By the time Hunter got to Los Angeles, her pattern of dating "creative types," as O'Brien put it, changed. She married lawyer Alexander Munro Hunter III, who is known as Kip. (In another brush with headlines, Kip Hunter's father was the district attorney in Boulder, Colo., during the investigation of the JonBenet Ramsey killing.)
They wed in August 1991, lived in Beverly Hills and divorced in 2000, according to their divorce records.
Hunter's divorce left her with $117,000 from the sale of the house and custody of 21 pieces of intellectual property -- possibly scripts or treatments -- with quirky titles including "Jupiter, Where Are You?", "So Very Virgo" and "How Did I Get Here?"
"She was always trying to get films done," recalled the friend.
As an actress, she had specks of roles in a few movies. In the 1991 film "Ricochet," she's the TV reporter who sticks a microphone in Denzel Washington's face. In 2000, she managed to get produced a comedy film short called "Billy Bob and Them." She wrote it and acted in it as well.
By late 2004, Hunter was back in New York. O'Brien reconnected with her that year at a 20th anniversary party for McInerney's famous first novel, "Bright Lights, Big City."
"She was very elegant," O'Brien said. The now-familiar photographs of Hunter in a lilac top, smiling broadly, were taken that night. With her blond hair and angular chin, she vaguely resembled Tory Burch, the socialite turned fashion designer.
O'Brien, then living in St. Louis, began helping Hunter long-distance with her spiritualism website. They spent hours on the phone, O'Brien said.
At first, Hunter did not reveal much about her new love in 2006.
It was John, Hunter said. He was from North Carolina and he was married and had little children.
They gave him the pet name "love lips."
That spring, O'Brien said, Hunter told her she might come to St. Louis to see "love lips" on "April 18 and 19."
"I was watching TV and I saw something -- 'John Edwards comes to Missouri,' " O'Brien said. "I thought, ohh, that's him."
Edwards spoke at the annual Public Affairs Conference at Missouri State University in Springfield on the evening of April 19, according to the school's website.
Ultimately, Hunter was hopeful they would end up together, said O'Brien: "She said he assured her she shouldn't have doubts."
O'Brien -- who never saw them together -- was surprised by her choice.